exo-3-Boc-3-azabicyclo[3.1.0]hexane-6-carbaldehyde

Base Information

• Chemical Name: exo-3-Boc-3-azabicyclo[3.1.0]hexane-6-carbaldehyde
• CAS No.: 419572-19-3
• Molecular Formula: C₁₁H₁₇NO₃
• Molecular Weight: 211.261
• Mol file: 419572-19-3.mol

Synonyms:(1α,5α,6α)-3-(tert-Butoxycarbonyl)-3-azabicyclo [3.1.0]hexane-6-carboxaldehyde

Chemical Property of exo-3-Boc-3-azabicyclo[3.1.0]hexane-6-carbaldehyde

Chemical Property:

• Boiling Point: 294.5±33.0 °C(Predicted)
• PKA: -1.53±0.40(Predicted)
• Density: 1.226±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

99%, ^*data from raw suppliers

Exo-3-Boc-3-azabicyclo[3.1.0]hexane-6-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of exo-3-Boc-3-azabicyclo[3.1.0]hexane-6-carbaldehyde

There total 7 articles about exo-3-Boc-3-azabicyclo[3.1.0]hexane-6-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(1R,5S,6r)-tert-butyl 6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (419572-18-2) → (1α,5α,6α)-3-(tert-Butoxycarbonyl)-3-azabicyclo [3.1.0]hexane-6-carboxaldehyde (419572-19-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmcl.2010.06.140

Reference yield:

oxalyl dichloride (79-37-8) + (1R,5S,6r)-tert-butyl 6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (419572-18-2) → (1α,5α,6α)-3-(tert-Butoxycarbonyl)-3-azabicyclo [3.1.0]hexane-6-carboxaldehyde (419572-19-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; ethyl acetate;

Reference yield:

(1α,5α,6α)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane (134575-13-6) → (1α,5α,6α)-3-(tert-Butoxycarbonyl)-3-azabicyclo [3.1.0]hexane-6-carboxaldehyde (419572-19-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water; 1,4-dioxane / 10 h / 20 - 30 °C

2: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1.5 h / -78 - 30 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; sodium hydroxide; In 1,4-dioxane; dichloromethane; water;

upstream raw materials:

(1R,5S,6r)-tert-butyl 6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate

oxalyl dichloride

(1α,5α,6α)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane

di-tert-butyl dicarbonate

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